Patent DE-102009058906-A1 (DE)
Title: New photochromic naphthopyran compounds useful as synthetic material such as ophthalmic lens and in sun glasses
Inventor: WEIGAND UDO
IPC: G02B5/23
Filed: 2009-12-18
Abstract: Photochromic naphthopyran compounds (Q), in which the aromatic substituent on the naphthalene ring of (I) and (II), which is located on the pyran ring, is connected to the second ring of naphthalene by a monoatomic carbon bridge, and the aromatic substituent on the naphthalene ring of (III), which is located on the pyran ring, is connected to the second naphthalene ring by a diatomic bridge, are new. Photochromic naphthopyran compounds (Q) of formula (I)-(III), in which the aromatic substituent on the naphthalene ring of (I) and (II), which is located on the pyran ring, is connected to the second ring of naphthalene by a monoatomic carbon bridge, and the aromatic substituent on the naphthalene ring of (III), which is located on the pyran ring, is connected to the second naphthalene ring by a diatomic bridge, are new. X : a diatomic bridge -O-CR 6>R 7>- or -CR 6>R 7>-O-, H, CH 3or C 6H 5; either R 6>, R 7>(hetero)aryl comprising phenyl, benzyl, phenoxy, benzyloxy, naphthoxy, phenanthryl, pyridyl, quinolyl, furanyl, thiophenyl, pyrrolyl, benzofuranyl, benzothiophenyl, indolyl or carbazolyl (all optionally mono- or di-substituted by (1-6C)-alkyl, (1-6C)-thioalkyl, (1-6C)-alkoxy, (3-7C)-cycloalkyl, Br Cl or F), or H or beta -group comprising phenyl, benzyl, phenoxy, benzyloxy, naphthyl, naphthoxy, phenanthryl (all optionally mono- or disubstituted by alpha group), (1-6C)-alkyl, (1-6C)-thioalkyl, (1-6C)-alkoxy, (3-7C)-cycloalkyl, Br, Cl, F, pyridyl, quinolyl, furanyl, thiophenyl, pyrrolyl, benzofuranyl, benzothiophenyl, indolyl or carbazolyl (for (III)); and R 1>0>, R 1>1>H or beta -group comprising (1-6C)-alkyl, (1-6C)-thioalkyl, (1-6C)-alkoxy, (3-7C)-cycloalkyl, Br, Cl, F, phenyl, benzyl, phenoxy, benzyloxy, naphthyl, naphthoxy or phenanthryl (all optionally mono- or di-substituted by alpha -group), pyridyl, quinolyl, furanyl, pyrrolyl, benzofuranyl, benzothiophenyl, indolyl or carbazolyl; or R 6>R 7>with spiro carbon atom, R 1>0R 1>1>with spiro carbon atom : 5-8 membered carbo or heteromonocyclic spiro ring containing non-adjacent one or two heteroatoms of O, S or N-R 8>, where: the two adjacent not spiro connected carbon atoms are again a part of a (hetero)aryl ring system, the ring systems is beta group comprising benzene, naphthalene, phenanthrene, pyridine, quinoline, furan, thiophene, pyrrole, benzofuran, benzothiophene, indole or carbazole (all optionally having one or two substituents) and the two adjacent annelated ring systems are optionally connected by an ortho, ortho'-bridge, or a 7-12-membered carbo-bicyclic ring or a 7-12-membered carbo-tricyclic ring (both optionally having 1-4 substituents of beta -group), provided that in (I) R 6>and R 7>under inclusion of the spiro-carbon atoms excludes cyclopentane or cyclohexane; R 1>H and beta -group consisting of comprising phenyl, benzyl, phenoxy, benzyloxy, naphthyl or naphthoxy (all optionally mono- or di-substituted by alpha -group), (1-6C)-alkyl, (1-6C)-thioalkyl, (1-6C)-alkoxy, or (3-7C)-cycloalkyl; R 8>H or a group X comprising (1-6C)-alkyl, (3-7C)-cycloalkyl, phenyl, benzyl or naphthyl (all mono- or di-substituted by alpha -group); either R 9>H or the group beta , which is optionally substituted by the alpha -group; or 2 ortho position R 9>an aromatic ring bonded -D 1>-(CH 2) k-E or -D 1>-(C(CH 3) 2) k-E-group, where the -D 1>-(CH 2) k-E- is optionally an annelated benzene ring; or 2R 9>benzene- or pyrido-ring (both optionally mono- or disubstituted by alpha -group); k : 1 or 2; D 1>, E : O, S, CH 2, C(CH 3) 2or C(C 6H 5) 2; either R 2>-R 5>H or alpha -group, where two ortho position of R 2>-R 5>residue bonded at the aromatic ring group forms -D ->(CH 2) k-E or -D 1>-(C(CH 3) 2) k-E; or R 2>R 3>, R 3>R 4>, R 5>R 2>, R 3>R 4>R 5>benzene- or pyrido-ring (both optionally mono- or di-substituted by the alpha group); m : 0-3; either B 1>, B 2>mono-, di- or trisubstituted aryl (preferably phenyl, naphthyl or phenanthryl), heteroaryl (preferably pyridyl, furanyl, benzofuranyl, thienyl, benzothienyl, 1,2,3,4-tetrahydrocarbazolyl or julolidinyl (all optionally mono- and di-substituted by the alpha group or delta group comprising OH, a phenyl ring (which is optionally mono- or di-substituted by 2-phenylethenyl, (phenylimino)methyl, (phenylmethylene)imino or mono- or diphenylamino)), amino, mono-(1-6C)-alkylamino, di-(1-6C)-alkylamino, piperidinyl, N-substituted piperazinyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, indolinyl, morpholinyl, 2,6-dimethylmorpholinyl, thiomorpholinyl, azacycloheptyl or azacyclooctyl), or phenothiazinyl, phenoxazinyl, 1,2,3,4-tetrahydroquinolinyl, 1,2,3,4-tetrahydroisoquinolinyl, phenazinyl, carbazolyl, 1,2,3,4-tetrahydrocarbazolyl or 10,11-dihydrodibenz[b, f]azepinyl (all optionally mono- or disubstituted by (1-6C)-alkyl, (1-6C)-alkoxy, Br, Cl or F), where two direct adjacent substituents of B 1>and B 2>represent a Y 1>-(CX 2) p-Z group, and two or more adjacent carbon atoms of Y 1>-(CX 2) p-Z can be an annelated benzene ring, which is optionally substituted by the alpha -group or delta -group; or B 1>B 2>C : optionally mono- or di-substituted 9,10-dihydroanthracene, F, thioxanthene, xanthene, benzo[b]fluorene, 5H-dibenzo[a, d]cycloheptene or dibenzosuberone residue or a saturated hydrocarbon, (3-12C)-spiro-monocyclic, (7-12C)-spiro-bicyclic, (7-12C)-spiro-tricyclic group, where the unsaturated cycle is optionally substituted by the alpha -group or delta -group; p : 1-3; and Y 1>, Z : O, S, N-(1-6C)-alkyl, N-C 6H 5, CH 2, C(CH 3) 2or C(C 6H 5) 2. 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